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Tip: Reserve the distillery tasting before lunch; the drive in on Old Frankfort Pike is the prettiest road in the Bluegrass.

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Frankfort (Buffalo Trace) ★ 4.5

Frankfort gives Lexington day-trippers free Buffalo Trace distillery tours, the state capitol and Rebecca Ruth's century-old bourbon ball candy kitchens.

Tip: Buffalo Trace tours are free but book out; reserve the Trace Tour early and save the gift shop for the end.

Winchester (Beer Cheese Country) ★ 4.4

Winchester claims beer cheese outright: a 13-stop trail, Ale-8-One's home town, and Hall's on the River standing where the Driftwood Inn invented the spread.

Tip: Do three or four trail stops then finish at Hall's on the River; pick up a cold Ale-8-One for the drive back.

Lawrenceburg (Wild Turkey and Four Roses) ★ 4.3

Lawrenceburg stacks two bourbon giants above the Kentucky River, with Wild Turkey's renovated visitor centre and Four Roses' distillery a short hop apart.

Tip: Wild Turkey runs Wednesday to Sunday; pair one big tour with the river overlook rather than forcing both in a day.

Harrodsburg and Shaker Village ★ 4.4

Harrodsburg holds the 1845 Beaumont Inn, a James Beard-honoured family table, with Shaker Village of Pleasant Hill's seed-to-table dining just up US-68.

Tip: The Old Owl Tavern side of Beaumont Inn takes walk-ins more easily than the main dining room on weekends.

Berea (Boone Tavern) ★ 4.2

Berea, Kentucky's folk arts and crafts capital, sends day-trippers to the 1909 Boone Tavern for farm-to-table dining amid Berea College's craft galleries.

Tip: Eat at Crafted at Boone Tavern, then walk the college square galleries; student artisans staff many of the studios.

Midway (Woodford County) ★ 4.6

Midway packs Ouita Michel's Holly Hill Inn, a 2025 James Beard semifinalist for hospitality, and a strollable rail-town main street 25 minutes from Lexington.

Tip: Book Holly Hill Inn for Saturday brunch, then walk the Railroad Street shops; trains still split the town centre.

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